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“Jack, take off your dress and panties,” I command in rising to unclip his leash.
What a look of panic! His blushing pink complexion deepens. He moves not.
“Show your mother that you are well kept... and cared for,” my tone firming.
He rises. As designed, Jack can by stripped naked in seconds. To obviate any further reluctance, I reach, grasp the straps of his dress at the shoulders and with a quick snap of the wrists and pull of my hands, whip the flimsy orange garment over his head. His hands obediently go to his head as he knows to step out of his sandals.
How many times has this scene been repeated, cleaning toilets almost daily in the nude?
Lastly I pull down his frilly panties from which he also steps out.
Jack stands before his stepmother, hairless body gleaming, muscle structure belying his effeminate attire. He’s an Adonis... with steel covered pubes.
“Remain standing. Let your mother look at you,” I command in picking up the clothing then returning to my chair.
“Makes quite the impression. And that cock cage is impressive as well. Paid for with trust funds I assume,” said Mrs. Lipton while gazing intently, certainly not shy about male nakedness.
“As I said, he’s denied sex. It is for the best.”
“I concur. Certainly would not want any more heirs... legitimate or otherwise.”
Jack begins to squirm. I know his exhibition, the excitement of being displayed, brings tumescence. Yes his penis is fighting its constraint, the erectile chambers flooding. He hates it... but he loves it. Ah the quandary of the masochist. And I understand it so well.
“Let’s talk about the will, Mrs. Lipton. Enough of stepson Jack.”
“What of it? It’s been probated. And a reasonable settlement made with Jack... and you as trustee.”
“Probated with you representing yourself as the wife of Mr. Lipton. Which you could not be if married to another. The Mexican divorce is a ruse, Mrs. Lipton. You’ve long known that.”
“You have nothing to gain in disclosing this. Jack is out. Only charity will benefit.”
“And I suspect be very aggressive in contesting the probate. All well funded charitable organizations with lots of lawyers... greedy lawyers. I have nothing to gain but you have much to lose.”
Mrs. Lipton returns to silence. I may be mistaken but there is joy in viewing Jack’s nakedness, seeming to ameliorate what I am sure is a most stressful conversation.
“More extortion. Just as I suspected.”
“You negotiated a little too hard with Jack’s penurious trust. You’re quite well off. Jack is not. And as you can now well imagine, he needs lots of care and attention due to his... proclivity.”
“I believ
e he’s in pain. Hate to think that I’m causing him discomfort,” the termagant twirling a finger in offering the same gesture... though there is nothing more to be removed... except...
“He’ll harden,” I forewarn, interpreting the motion of her finger.
“So be it. Make the poor boy comfortable.”
Jack’s key resides about my neck as always. But I must look to my bag. Returning the Prince’s Wand requires KY jelly, otherwise the reinsertion isn’t painful, it’s torture. Yes, I have small tube!
“Come here, Jack,” his stunned look silently pleading with me.
No mercy.
“Any arrangement we agree to will involve me taking over Jack’s care, Miss Kelly. That must be understood from the start. I will not be had a third time.”
“It’s burdensome, Mrs. Lipton. Keeping a male in chastity will require much of your time and attention.”
“I have a special place in mind for Jack. It will not be my time... it will involve my money... and that I have lots of.”
